槐庶尺蛾性信息素腺体EAG活性成分绝对构型的鉴定(英文)  

Determination of the absolute configuration of an EAG active component in the sex pheromone gland of Semiothisa cinerearia Bremer et Grey (Lepidoptera:Geometridae)

作　　者：孔祥波[1] 王鸿斌[1] 张真[1] 

机构地区：[1]中国林业科学研究院森林生态环境与保护研究所,国家林业局森林保护重点实验室,北京100091

出　　处：《昆虫学报》2012年第2期162-167,共6页Acta Entomologica Sinica

基　　金：国家自然科学基金项目(30771737);中央级公益性科研院所基本科研业务费专项资金项目(CAFRIFEEP201002)

摘　　要：槐庶尺蛾Semiothi sacinerearia Bremer et Grey(鳞翅目:尺蛾科)是我国北方国槐Sophora japonica L.上的重要食叶害虫。本研究的主要目的是阐明槐庶尺蛾性信息素成分化学结构的绝对构型,为在城市地区环境友好地防控槐庶尺蛾的为害提供一种新方法。经与标准品比较气相色谱保留时间和质谱特征离子,从槐庶尺蛾处女雌蛾(2-3日龄)性信息素腺体溶剂提取物中检测到顺6,顺9-顺-3,4-环氧-十七碳二烯烃和顺3,顺6,顺9-3,6,9-十七碳三烯烃2种成分,在腺体中以100∶4.8±1.3(N=12)的比例存在。槐庶尺蛾性信息素腺体提取物进一步经手性毛细管色谱柱(CycloSil-B,30m×0.25mm×0.25μm液膜厚)分离,在优化的程序升温条件下发现腺体成分顺6,顺9-顺-3,4-环氧-十七碳二烯烃具有3R,4S的绝对构型。两种合成的对映异构体混合物顺6,顺9-3R,4S-环氧-十七碳二烯烃和顺6,顺9-3S,4R-环氧-十七碳二烯烃以1.28∶1的比例加到腺体提取物中,比例变为1.55∶1。根据这一分析,腺体成分顺6,顺9-顺-3,4-环氧-十七碳二烯烃进一步确认具有3R,4S的绝对构型。该研究结论将为生产上研发高效的槐庶尺蛾性信息素诱芯奠定坚实的基础。The Chinese scholar tree looper, Semiothisa cinerearia Bremer et Grey （Lepidoptera： Geometridae）, is the major defoliator of the Chinese scholar tree Sophora japonica L. in China. The elucidation of the absolute chemical structure of the sex pheromone component of S. cinerearia may provide a potential chemical for the pest control against the S. cinerearia infestations in the urban area. In this study, two sex pheromone gland compounds, i.e. , （6Z, 9Z）-6, 9-cis-3, 4-epoxy-heptadecadiene （6Z, 9Z-cis-3, 4-epoxy-17： H） and （3Z, 6Z, 9Z）-3, 6, 9-heptadecatriene （3Z, 6Z, 9Z-17： H）, were detected in a 100∶ 4.8±1.3 ratio （N=12） during analyses of solvent extracts from virgin female S. cinerearia （2-3 d old） by comparison of their gas chromatography （GC） retention time and mass spectra （MS） with those of synthetic standards. Furthermore, the absolute configuration of 6Z, 9Z-cis-3, 4-epoxy-17： H in the sex pheromone gland of S. cinerearia was determined as （6Z, 9Z）-3R, 4S-epoxy-heptadecadiene by using a chiral capillary column （CycloSil-B, 30 m × 0.25 mm × 0.25 μm film） GC under the optimized oven temperature program. The mixture of the two synthetic enantiomers of 6Z, 9Z-3R, 4S-epoxy-17： H and 6Z, 9Z-3S, 4R-epoxy-17： H in a ratio of 1.28∶ 1 was injected into the female extracts, and thus the ratio was changed to 1.55∶ 1. Based on this analysis, the absolute configuration of the gland component 6Z, 9Z-cis-3, 4-epoxy-17：H was further confirmed as 3R, 4S. It is anticipated that control of S. cinerearia infestation with enantiomerically pure materials will be much more effective.

关 键 词：槐庶尺蛾 性信息素 顺6 顺9-3R 4S-环氧-十七碳二烯烃 绝对构型 气相色谱-质谱 手性分离 

分 类 号：Q968[生物学—昆虫学]